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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Home in Great Barrington
Renovated Downtown Great Barrington House
3 bedrooms, 4 beds, 2 private bathrooms
28 Sept – 3 Oct
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4.99 out of 5 average rating, 76 reviews
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds
10–15 Sept
4.97 out of 5 average rating, 141 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
13–18 Sept
4.95 out of 5 average rating, 175 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
20–25 Sept
4.92 out of 5 average rating, 193 reviews
Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 56 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds
10–15 Sept
4.87 out of 5 average rating, 31 reviews
Top guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds
10–15 Sept
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Great Barrington
Charming, view, large deck, private/walk downtown
3 bedrooms, 4 beds
10–15 Sept
4.89 out of 5 average rating, 101 reviews
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 queen beds
26–31 Oct
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Home in Great Barrington
Walk to Town! Great Barrington 4-bedroom farmhouse
4 bedrooms, 4 beds
26–31 Oct
5.0 out of 5 average rating, 116 reviews
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds
25–30 Oct
4.93 out of 5 average rating, 158 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds
10–15 Sept
4.78 out of 5 average rating, 101 reviews
Guest favourite
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
4 bedrooms, 6 beds
10–15 Sept
4.94 out of 5 average rating, 84 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds
10–15 Sept
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds
11–16 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Great Barrington
Modern Victorian- Walk to Town
4 bedrooms, 7 beds
14–19 Sept
4.97 out of 5 average rating, 142 reviews
Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds
13–18 Sept
4.94 out of 5 average rating, 88 reviews
Top guest favourite
Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds
13–18 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 8 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 67 reviews